Ogipeptin A

Details

• Internal ID: c781ed73-d1af-4285-bba5-3f4d2347828d
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Cyclic peptides
• IUPAC Name: N-[(3S,6S,9S,12S,15S,21S,22R)-15-(2-aminoethyl)-6-[(1R)-2-amino-1-hydroxyethyl]-3-[(1S)-2-amino-1-hydroxyethyl]-9-[3-(diaminomethylideneamino)propyl]-18-ethylidene-22-hydroxy-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]decanamide
• SMILES (Canonical): CCCCCCCCCC(=O)NC1C(CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(=CC)NC1=O)CCN)CC(C)C)CCCN=C(N)N)C(CN)O)C(CN)O)O
• SMILES (Isomeric): CCCCCCCCCC(=O)N[C@H]1[C@@H](CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C(=CC)NC1=O)CCN)CC(C)C)CCCN=C(N)N)[C@@H](CN)O)[C@H](CN)O)O
• InChI: InChI=1S/C42H78N14O11/c1-5-7-8-9-10-11-12-15-31(60)54-34-30(59)22-49-39(65)32(28(57)20-44)56-41(67)33(29(58)21-45)55-37(63)25(14-13-18-48-42(46)47)51-38(64)27(19-23(3)4)53-36(62)26(16-17-43)52-35(61)24(6-2)50-40(34)66/h6,23,25-30,32-34,57-59H,5,7-22,43-45H2,1-4H3,(H,49,65)(H,50,66)(H,51,64)(H,52,61)(H,53,62)(H,54,60)(H,55,63)(H,56,67)(H4,46,47,48)/t25-,26-,27-,28-,29+,30+,32-,33-,34-/m0/s1
• InChI Key: VMDXXLVULZDQNB-ZBQMFOSJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₈N₁₄O₁₁
• Molecular Weight: 955.20 g/mol
• Exact Mass: 954.59744936 g/mol
• Topological Polar Surface Area (TPSA): 436.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -5.37
• H-Bond Acceptor: 15
• H-Bond Donor: 16
• Rotatable Bonds: 21

Synonyms

• N-[(3S,6S,9S,12S,15S,21S,22R)-15-(2-aminoethyl)-6-[(1R)-2-amino-1-hydroxyethyl]-3-[(1S)-2-amino-1-hydroxyethyl]-9-[3-(diaminomethylideneamino)propyl]-18-ethylidene-22-hydroxy-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]decanamide
• N-((3S,6S,9S,12S,15S,21S,22R)-15-(2-aminoethyl)-6-((1R)-2-amino-1-hydroxyethyl)-3-((1S)-2-amino-1-hydroxyethyl)-9-(3-(diaminomethylideneamino)propyl)-18-ethylidene-22-hydroxy-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl)decanamide
• N-((3S,6S,9S,12S,15S,21S,22R)-6-((1R)-2-Amino-1-hydroxyethyl)-3-((1S)-2-amino-1-hydroxyethyl)-15-(2-aminoethyl)-9-(3-carbamimidamidopropyl)-18-ethylidene-2,5,8,11,14,17,20,22-octahydroxy-12-(2-methylpropyl)-1,4,7,10,13,16,19-heptaazacyclotricosa-1,4,7,10,13,16,19-heptaen-21-yl)decanimidate
• N-[(3S,6S,9S,12S,15S,21S,22R)-6-[(1R)-2-Amino-1-hydroxyethyl]-3-[(1S)-2-amino-1-hydroxyethyl]-15-(2-aminoethyl)-9-(3-carbamimidamidopropyl)-18-ethylidene-2,5,8,11,14,17,20,22-octahydroxy-12-(2-methylpropyl)-1,4,7,10,13,16,19-heptaazacyclotricosa-1,4,7,10,13,16,19-heptaen-21-yl]decanimidate
• RefChem:167978
• CHEBI:225683

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8098	80.98%
Caco-2	-	0.8627	86.27%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6811	68.11%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.8262	82.62%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7745	77.45%
P-glycoprotein inhibitior	+	0.7406	74.06%
P-glycoprotein substrate	+	0.8701	87.01%
CYP3A4 substrate	+	0.6955	69.55%
CYP2C9 substrate	-	0.6060	60.60%
CYP2D6 substrate	-	0.8163	81.63%
CYP3A4 inhibition	-	0.8852	88.52%
CYP2C9 inhibition	-	0.8369	83.69%
CYP2C19 inhibition	-	0.8136	81.36%
CYP2D6 inhibition	-	0.8978	89.78%
CYP1A2 inhibition	-	0.8568	85.68%
CYP2C8 inhibition	+	0.6613	66.13%
CYP inhibitory promiscuity	-	0.9873	98.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5712	57.12%
Eye corrosion	-	0.9811	98.11%
Eye irritation	-	0.8997	89.97%
Skin irritation	-	0.7514	75.14%
Skin corrosion	-	0.9127	91.27%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4443	44.43%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.6626	66.26%
skin sensitisation	-	0.8275	82.75%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.8424	84.24%
Acute Oral Toxicity (c)	III	0.6349	63.49%
Estrogen receptor binding	+	0.7793	77.93%
Androgen receptor binding	+	0.6087	60.87%
Thyroid receptor binding	-	0.5132	51.32%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6708	67.08%
PPAR gamma	+	0.7340	73.40%
Honey bee toxicity	-	0.7834	78.34%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6124	61.24%
Fish aquatic toxicity	+	0.6551	65.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.81%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.50%	96.09%
CHEMBL299	P17252	Protein kinase C alpha	99.46%	98.03%
CHEMBL230	P35354	Cyclooxygenase-2	98.63%	89.63%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.11%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.89%	98.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	96.77%	92.88%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.11%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.00%	96.61%
CHEMBL2996	Q05655	Protein kinase C delta	94.95%	97.79%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	93.92%	90.71%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.89%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	93.78%	96.47%
CHEMBL221	P23219	Cyclooxygenase-1	93.43%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.19%	99.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	93.02%	97.29%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	91.51%	96.11%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	90.65%	95.71%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	90.54%	91.03%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	89.62%	96.90%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.36%	100.00%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	88.35%	92.32%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.93%	100.00%
CHEMBL255	P29275	Adenosine A2b receptor	87.79%	98.59%
CHEMBL3038469	P24941	CDK2/Cyclin A	87.52%	91.38%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	87.44%	92.86%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.34%	85.14%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.23%	90.08%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.96%	91.24%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.76%	93.03%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	86.32%	95.58%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.28%	95.50%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.18%	89.34%
CHEMBL1937	Q92769	Histone deacetylase 2	85.23%	94.75%
CHEMBL2208	P49137	MAP kinase-activated protein kinase 2	85.03%	95.20%
CHEMBL4588	P22894	Matrix metalloproteinase 8	84.73%	94.66%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	84.41%	96.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.34%	82.69%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.77%	98.75%
CHEMBL4581	P52732	Kinesin-like protein 1	82.55%	93.18%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.78%	83.10%
CHEMBL222	P23975	Norepinephrine transporter	81.76%	96.06%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	81.70%	95.00%
CHEMBL2514	O95665	Neurotensin receptor 2	80.95%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	80.60%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.17%	89.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139589390
• LOTUS: LTS0260763
• wikiData: Q105288929